Cefixime trihydrateProduct ingredient for Cefixime
- Name
- Cefixime trihydrate
- Drug Entry
- Cefixime
Bacteria possess a cell wall comprising a glycopeptide polymer commonly known as peptidoglycan, which is synthesized and remodelled through the action of a family of enzymes known as "penicillin-binding proteins" (PBPs).8 β-lactam antibiotics, including cephalosporins, are PBP inhibitors that, through inhibition of essential PBPs, result in impaired cell wall homeostasis, loss of cell integrity, and ultimately bacterial cell death.8,9,10 Cefixime is a broad-spectrum antibiotic and an orally-active third-generation semisynthetic cephalosporin.3,15,21 Cephalosporins are beta-lactam antibiotics and can be used to treat gram-positive and gram-negative bacterial infections which include conditions such as skin infections, resistant bacteria, and meningitis.12 Examples of third-generation cephalosporins are ceftriaxone, cefotaxime, and ceftazidime.12
Third-generation cephalosporins are often a first-line therapy against certain bacterial infections.17 However, cefixime is not recommended as a first-line of treatment for uncomplicated urogenital, anorectal, or pharyngeal gonorrhea because cefixime does not provide the same bactericidal effect as ceftriaxone.24,16 Generally, cefixime is used to treat uurinary tract infections, middle ear infections, pharyngitis, tonsillitis, exacerbations of chronic bronchitis, and uncomplicated gonorrhea.21 The beta-lactam ring of cefixime inhibits bacterial cell wall synthesis by binding to the penicillin-binding proteins which will then result in lysis.12,7,6 Specifically, cephalosporins inhibit penicillin-sensitive enzymes responsible for the final 3D structure of the bacterial cell wall which in turn inhibit bacterial cell wall peptidoglycan synthesis.19,20 Additionally, third-generation cephalosporins have been shown to have more stability in the presence of beta-lactamases compared to first- and second-generation cephalosporins.18 Cefixime was first approved in the United States in 1986.21
- Accession Number
- DBSALT001818
- Structure
- Synonyms
- Not Available
- UNII
- 97I1C92E55
- CAS Number
- 125110-14-7
- Weight
- Average: 507.49
Monoisotopic: 507.072984244 - Chemical Formula
- C16H21N5O10S2
- InChI Key
- IPYWNMVPZOAFOQ-NABDTECSSA-N
- InChI
- InChI=1S/C16H15N5O7S2.3H2O/c1-2-6-4-29-14-10(13(25)21(14)11(6)15(26)27)19-12(24)9(20-28-3-8(22)23)7-5-30-16(17)18-7;;;/h2,5,10,14H,1,3-4H2,(H2,17,18)(H,19,24)(H,22,23)(H,26,27);3*1H2/b20-9-;;;/t10-,14-;;;/m1.../s1
- IUPAC Name
- (6R,7R)-7-[(2Z)-2-(2-amino-1,3-thiazol-4-yl)-2-[(carboxymethoxy)imino]acetamido]-3-ethenyl-8-oxo-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylic acid trihydrate
- SMILES
- O.O.O.NC1=NC(=CS1)C(=N\OCC(O)=O)\C(=O)N[C@H]1[C@H]2SCC(C=C)=C(N2C1=O)C(O)=O
- External Links
- ChemSpider
- 4590586
- Predicted Properties
Property Value Source Water Solubility 0.104 mg/mL ALOGPS logP 0.25 ALOGPS logP -1.6 Chemaxon logS -3.6 ALOGPS pKa (Strongest Acidic) 3.45 Chemaxon pKa (Strongest Basic) 2.92 Chemaxon Physiological Charge -2 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 184.51 Å2 Chemaxon Rotatable Bond Count 8 Chemaxon Refractivity 104.91 m3·mol-1 Chemaxon Polarizability 41.59 Å3 Chemaxon Number of Rings 3 Chemaxon Bioavailability 1 Chemaxon Rule of Five No Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule Yes Chemaxon